Sulfanilamide → HCID 178512699, compound

HRID 894313Notes

Reaction equation

HRID 894313 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][C:14](=[NH:17])OC)[N:9]=1)[C:2]([NH2:4])=[NH:3].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(O)C>[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:14](=[NH:17])[CH2:13][CH2:12][S:11][CH2:10][C:8]2[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=2)(=[O:26])=[O:27])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 5333SulfanilamideHCID 12881442Methyl 3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]propanimidate

Product 1

HCID 178512699HCID 178512699, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 10 ml of ethanol were dissolved 1 g of methyl 3-[(2-guanidinothiazol-4-yl)methylthio]propionimidate and 0.69 g p-aminobenzenesulfonamide and after causing reaction for 48 hours at room temperature, the solvent was distilled off under reduced pressure. Then, the residue formed was purified by a silica gel column chromatography using a mixture of chloroform and methanol (20:1→10:1) to provide 1.2 g N-(p-aminobenzenesulfonyl)-3-[(2-guanidinothiazol-4-yl)methylthio]propionamidine as an amorphous solid. The product shows the following physicochemical properties.

Workup

  1. customreaction for 48 hours at room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThen, the residue formed
  4. customwas purified by a silica gel column chromatography
  5. additiona mixture of chloroform and methanol (20:1→10:1)

Sources & evidence

ORD record
ord-33fd1d93da0d4ef4b7d524e6df0ac4eb
Source dataset
uspto-grants-1981_08
Patent number
US04283408

Reaction notes

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